N-(substituted amino)imide derivatives, preparation process thereof, and herbicidal composition

ABSTRACT

An N-(substituted amino)imide derivative represented by the formula (I) is a novel compound which can be utilized as an effective ingredient of herbicidal compositions. ##STR1## wherein, R 1  is hydrogen atom, C 1  -C 4  alkyl group, C 7  -C 9  aralkyl group, C 1  -C 4  haloalkyl group, (C 1  -C 4  alkyl)carbonyl group or (C 1  -C 4  alkyl)sulfonyl group; 
     A represents a structure selected from the group consisting of the following formulas (A-1), (A-2), (A-3), (A-4) and (A-5) ##STR2##  wherein R 2  and R 3  in the formula (A-1) are independently hydrogen atom or C 1  -C 4  alkyl group, but not R 2  =R 3  =H, R 4  in the formula (A-4) is halogen atom, C 1  -C 4  alkyl group and/or nitro group, m is an integer of 0-4, the substituents of m not less than 2 being same or different; 
     X 1  and X 2  are independently hydrogen atom, halogen atom, C 1  -C 4  alkyl group, C 1  -C 4  alkoxy group, C 1  -C 4  alkylthio group, C 1  -C 4  haloalkyl group, C 1  -C 4  haloalkoxy group, C 1  -C 4  haloalkylthio group, C 2  -C 4  alkoxyalkyl group, C 2  -C 4  thioalkoxyalkyl group or NR 7  R 8 , wherein R 7  and R 8  are independently hydrogen atom, C 1  -C 4  alkyl group or C 1  -C 4  alkoxy group; and 
     Z is nitrogen atom or CH.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to N-(substituted amino)imide derivatives, production process thereof, and 4herbicides containing the derivatives as active ingredients.

2. Description of the Related Arts

Regarding herbicidal compounds having an (azinylureylene)sulfonyl group such as a { (pyrimidin-2-yl-or 1,3,5-triazin-2-yl)aminocarbonyl!aminosulfonyl} group, a variety of compounds has heretofore been reported. For example, there are following reports regarding atoms to which an (azinylureylene)sulfonyl group is attached.

U.S. Pat. No. 4,169,719: Carbon atoms in a nonsubstituted or substituted benzene ring.

EP-A-51466: α-Carbon atom in the unsubstituted or substituted toluene.

U.S. Pat. No. 4,473,394: Carbon atom in the unsubstituted or substituted pyrrole ring.

GB 2,015,503 and EP-A-98569: Oxygen atom of hydroxyl group in unsubstituted or substituted phenols.

U.S. Pat. No. 4,440,565: Oxygen atom of hydroxyl group in unsubstituted or substituted alcohols.

U.S. Pat. No. 4,601,747 and U.S. Pat. No. 4,718,937: Nitrogen atom of the alkanesulfonamide group or alkoxyamino group.

U.S. Pat. No. 4,515,620: Nitrogen atom of the amino group in substituted anilines or 1-aminoindanes.

GB Patent 2,110,689: Nitrogen atom in the ring of pyrrolidine, piperidine, morpholine,thiomorpholine or 1,3-thiazolidine.

Among herbicidal compounds described in the above patent publications, compounds having an (azinylureylene)sulfonyl group such as { (pyrimidin-2-yl-or 1,3,5-triazin-2-yl)aminocarbonyl!aminosulfonyl} group on a nitrogen atom of the nitrogen containing heterocyclic ring have been known (GB 2,110,689), but compounds having an (azinylureylene)sulfonyl group which is attached to a nitrogen atom of the imide group through another nitrogen atom have not be known.

By the way, there have conventionally been strong demands for herbicides capable of exhibiting reliable herbicidal activity even at such low application dosages as bringing about the advantage of reducing the amount present in the environment, herbicides capable of exhibiting selectivity between crops and weeds irrespective of variations in environmental conditions, herbicides free from crop injury to the second crop in double cropping, etc.

The present invention has been completed with a view toward meeting such demands.

Thus the present inventors have found that compounds having an (azinylureylene)sulfonyl group which is attached to a nitrogen atom of the imide group through another nitrogen atom have excellent herbicidal activity, leading to the completion of the present invention.

SUMMARY OF THE INVENTION

Therefore, an object of the present invention is to provide novel compounds exhibiting excellent herbicidal activity, to provide a preparation process thereof, to provide novel herbicidal compositions containing one or more of the derivatives as active ingredients, and to intermediate compounds thereof.

The present invention has the following constructive features.

In the first aspect of the invention, there is thus provided an N-(substituted amino)imide derivative represented by the formula (I). ##STR3## wherein, R¹ is hydrogen atom, C₁ -C₄ alkyl group, C₇ -C₉ aralkyl group, C₁ -C₄ haloalkyl group, (C₁ -C₄ alkyl)carbonyl group or (C₁ -C₄ alkyl)sulfonyl group;

A represents a structure selected from the group consisting of the following formulas (A-1), (A-2), (A-3), (A-4) and (A-5) ##STR4## wherein R² and R³ in the formula (A-1) are independently hydrogen atom or C₁ -C₄ alkyl group, but not R² ═R³ ═H, R⁴ in the formula (A-4) is halogen atom, C₁ -C₄ alkyl group and/or nitro group, m is an integer of 0-4, the substituents of m not less than 2 being same or different;

X¹ and X² are independently hydrogen atom, halogen atom, C₁ -C₄ alkyl group, C₁ -C₄ alkoxy group, C₁ -C₄ alkylthio group, C₁ -C₄ haloalkyl group, C₁ -C₄ haloalkoxy group, C₁ -C₄ haloalkylthio group, C₂ -C₄ alkoxyalkyl group, C₂ -C₄ thioalkoxyalkyl group or NR⁷ R⁸, wherein R⁷ and R⁸ are independently hydrogen atom, C₁ -C₄ alkyl group or C₁ -C₄ alkoxy group; and

Z is nitrogen atom or CH.

In the second aspect of the invention, there is provided a process for preparation of the above N-(substituted amino) imide derivative represented by the formula (I-a), which comprises reacting an N-aminoimide derivative of the formula (II-a) with an (azinylureylene)sulfonyl halide of the formula (III):

according to the following reaction formula: ##STR5## wherein Aa is a structure selected from the group consisting of the above-mentioned formulas (A-1), (A-2), (A-3) and (A-4), X¹, X² and Z have each the same meaning as defined above, and y₁ is halogen atom.

In the third aspect of the invention, there is provided a process for preparation of an N-(substituted amino)imide derivative represented by the formula (I-b1), which comprises reacting an N-(substituted amino)imide derivative of the formula (I-b2) with a compound represented by the formula (IV) in the presence of a base to replace the hydrogen atom on N-amino group with R¹ b according to the following reaction formula: ##STR6## wherein Aa is a structure selected from the group consisting of the above-mentioned formulas (A-1), (A-2), (A-3) and (A-4), X¹, X², Z and m have each the same meaning as defined above, R¹ b is C₁ -C₄ alkyl group, C₇ -C₉ aralkyl group, C₁ -C₄ haloalkyl group, (C₁ -C₄ alkyl)carbonyl group or (C₁ -C₄ alkyl)sulfonyl group, and y₂ is halogen atom or (C₁ -C₄ alkyl)carbonyl!oxy group.

In the fourth aspect of the invention, there is provided a process for preparation of an N-(substituted amino)imide derivative of the formula (I-c1), which comprises pyrolysis of an N-(substituted amino)imide derivative of the formula (I-c2) according to the following reaction formula: ##STR7## wherein R¹ c is C₁ -C₄ alkyl group, C₇ -C₉ aralkyl group or C₁ -C₄ haloalkyl group, X¹, X² and Z have each the same meaning as defined above.

In the fifth aspect of the invention, there is provided a herbicidal agent which comprises a herbicidally effective amount of an N-(substituted amino)imide derivative of the above-mentioned formula (I) as an active ingredient.

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

In the description hereinafter, A, Aa, A-1- A-5, R¹ -R⁴, R¹ b, R¹ c, X¹, X² , Z m, y₁ and y₂ in the above formulas have each the same meaning as defined above. C₁ -C₄ alkyl in R² and R³ includes methyl and ethyl. Halogen in R⁴ includes fluorine, chlorine, bromine and idodine. C₁ -C₄ alkyl in R⁴ includes methyl and ethyl.

Specific examples of the derivatives of the above formula (I) according to the present invention include those shown in Table 1-Table 9. In the tables, CH₂ Ph means benzyl group.

                  TABLE 1                                                          ______________________________________                                         No.  A          R.sup.1                                                                              X.sup.1    X.sup.2   Z                                   ______________________________________                                         I-I  In compounds                                                                              H     CF.sub.3   OCH.sub.3 CH                                  I-2  No. I-1-   H     CF.sub.3   OCHF.sub.2                                                                               CH                                  I-3  No. I-168, H     CH(CH.sub.3).sub.2                                                                        OCH.sub.3 CH                                  I-4  the group A is                                                                            H     CH(OCH.sub.3).sub.2                                                                       CH.sub.3  CH                                  I-5  A-1(R.sup.2 = R.sup.3 =                                                                   H     CH.sub.2 F OCH.sub.3 CH                                  I-6  CH.sub.3)  H     CH.sub.2 F OCHF.sub.2                                                                               CH                                  I-7             H     CH.sub.2 OCH.sub.3                                                                        CH.sub.3  CH                                  I-11            H     CH.sub.2 OCH.sub.3                                                                        OCH.sub.3 CH                                  I-12            H     CH.sub.2 OCH.sub.3                                                                        OCHF.sub.2                                                                               CH                                  I-13            H     CH.sub.3   CF.sub.3  CH                                  I-14            H     CH.sub.3   CH.sub.3  CH                                  I-15            H     CH.sub.3   Cl        CH                                  I-16            H     CH.sub.3   F         CH                                  I-17            H     CH.sub.3   H         CH                                  I-21            H     CH.sub.3   OC.sub.2 H.sub.5                                                                         CH                                  I-22            H     CH.sub.3   OCF.sub.2 CHF.sub.2                                                                      CH                                  I-23            H     CH.sub.3   OCF.sub.2 CHFCF.sub.3                                                                    CH                                  I-24            H     CH.sub.3   OCH.sub.2 CF.sub.3                                                                       CH                                  I-25            H     CH.sub.3   OCH.sub.2 CH.sub.2 F                                                                     CH                                  I-26            H     CH.sub.3   OCH.sub.2 CHF.sub.2                                                                      CH                                  I-27            H     CH.sub.3   OCH.sub.3 CH                                  I-31            H     CH.sub.3   OCHF.sub.2                                                                               CH                                  I-32            H     CH.sub.3   SCH.sub.3 CH                                  I-33            H     CHF.sub.2  CH.sub.3  CH                                  I-34            H     Cl         Cl        CH                                  I-35            H     Cl         H         CH                                  I-36            H     Cl         N(CH.sub.3).sub.2                                                                        CH                                  I-37            H     Cl         NH.sub.2  CH                                  I-41            H     Cl         OC.sub.2 H.sub.5                                                                         CH                                  I-42            H     Cl         OCF.sub.2 CHF.sub.2                                                                      CH                                  I-43            H     Cl         OCF.sub.2 CHFCl                                                                          CH                                  I-44            H     Cl         OCH.sub.3 CH                                  I-45            H     Cl         OCHF.sub.2                                                                               CH                                  I-46            H     N(CH.sub.3).sub.2                                                                         OCF.sub.2 CHF.sub.2                                                                      CH                                  I-47            H     N(CH.sub.3).sub.2                                                                         OCH.sub.3 CH                                  I-51            H     N(CH.sub.3).sub.2                                                                         OCHF.sub.2                                                                               CH                                  I-52            H     N(CH.sub.3).sub.2                                                                         SCHF.sub.2                                                                               CH                                  I-53            H     N(CH.sub.3)C.sub.2 H.sub.5                                                                OCHF.sub.2                                                                               CH                                  I-54            H     N(CH.sub.3)OCH.sub.3                                                                      OCHF.sub.2                                                                               CH                                  I-55            H     NH.sub.2   OCH.sub.3 CH                                  I-56            H     NHCH.sub.3 OCH.sub.3 CH                                  I-57            H     NHCH.sub.3 OCHF.sub.2                                                                               CH                                  I-61            H     OC.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.5                                                                         CH                                  I-62            H     OCF.sub.2 CHF.sub.2                                                                       SCH.sub.3 CH                                  I-63            H     OCH(CH.sub.3).sub.2                                                                       OCHF.sub.2                                                                               CH                                  I-64            H     OCH.sub.2 CF.sub.3                                                                        OCH.sub.3 CH                                  I-65            H     OCH.sub.2 CH.sub.2 F                                                                      OCH.sub.3 CH                                  I-66            H     OCH.sub.2 CHF.sub.2                                                                       OCH.sub.3 CH                                  I-67            H     OCH.sub.3  OC.sub.2 H.sub.5                                                                         CH                                  I-71            H     OCH.sub.3  OCF.sub.2 CHF.sub.2                                                                      CH                                  I-72            H     OCH.sub.3  OCF.sub.2 CHFCF.sub.3                                                                    CH                                  I-73            H     OCH.sub.3  OCH(CH.sub.3).sub.2                                                                      CH                                  I-74            H     OCH.sub.3  OCH.sub.3 CH                                  I-75            H     OCH.sub.3  SCH.sub.3 CH                                  I-76            H     OCH.sub.3  SCHF.sub.2                                                                               CH                                  I-77            H     OCHF.sub.2 OCH.sub.2 CF.sub.3                                                                       CH                                  I-81            H     OCHF.sub.2 OCH.sub.2 CH.sub.3                                                                       CH                                  I-82            H     OCHF.sub.2 OCH.sub.3 CH                                  I-83            H     OCHF.sub.2 OCHF.sub.2                                                                               CH                                  I-84            H     OCHF.sub.2 SCH.sub.3 CH                                  I-85            H     C.sub.2 H.sub.5                                                                           OCH.sub.3 N                                   I-86            H     C.sub.2 H.sub.5                                                                           SCH.sub.3 N                                   I-87            H     CF.sub.3   OCH.sub.3 N                                   I-91            H     CH(CH.sub.3).sub.2                                                                        CH.sub.3  N                                   I-92            H     CH(CH.sub.3).sub.2                                                                        Cl        N                                   I-93            H     CH(CH.sub.3).sub.2                                                                        OCH.sub.3 N                                   I-94            H     CH(CH.sub.3).sub.2                                                                        SCH.sub.3 N                                   I-95            H     CH.sub.2 CF.sub.3                                                                         CH.sub.3  N                                   I-96            H     CH.sub.2 F CH.sub.3  N                                   I-97            H     CH.sub.2 F OCH.sub.3 N                                   I-101           H     CH.sub.2 OCH.sub.3                                                                        CH.sub.3  N                                   I-102           H     CH.sub.2 OCH.sub.3                                                                        OCH.sub.3 N                                   I-103           H     CH.sub.2 SCH.sub.3                                                                        CH.sub.3  N                                   I-104           H     CH.sub.2 SCH.sub.3                                                                        Cl        N                                   I-105           H     CH.sub.2 SCH.sub.3                                                                        OC.sub.2 H.sub.5                                                                         N                                   I-106           H     CH.sub.2 SCH.sub.3                                                                        OCH.sub.3 N                                   I-107           H     CH.sub.2 SCH.sub.3                                                                        SCH.sub.3 N                                   I-111           H     CH.sub.3   CF.sub.3  N                                   I-112           H     CH.sub.3   CH.sub.3  N                                   I-113           H     CH.sub.3   Cl        N                                   I-114           H     CH.sub.3   F         N                                   I-115           H     CH.sub.3   H         N                                   I-116           H     CH.sub.3   OCH.sub.2 CF.sub.3                                                                       N                                   I-117           H     CH.sub.3   OCH.sub.2 CH.sub.2 F                                                                     N                                   I-121           H     CH.sub.3   OCH.sub.2 CHF.sub.2                                                                      N                                   I-122           H     CH.sub.3   OCH.sub.3 N                                   I-123           H     CH.sub.3   SCH.sub.3 N                                   I-124           H     CH.sub.3   SCHF.sub.2                                                                               N                                   I-125           H     CHF.sub.2  CH.sub.3  N                                   I-126           H     CHF.sub.2  OCH.sub.3 N                                   I-127           H     Cl         Cl        N                                   I-131           H     Cl         OCH(CH.sub.3).sub.2                                                                      N                                   I-132           H     Cl         OCH.sub.2 CF.sub.3                                                                       N                                   I-133           H     Cl         OCH.sub.3 N                                   I-134           H     Cl         SCH.sub.3 N                                   I-135           H     F          OCH.sub.3 N                                   I-136           H     H          NH(CH.sub.3)                                                                             N                                   I-137           H     N(CH.sub.3).sub.2                                                                         OCH.sub.3 N                                   I-141           H     N(CH.sub.3).sub.2                                                                         SCHF.sub.2                                                                               N                                   I-142           H     NHCH.sub.3 OCH.sub.3 N                                   I-143           H     OC.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.5                                                                         N                                   I-144           H     OCF.sub.2 CHF.sub.2                                                                       SCH.sub.3 N                                   I-145           H     OCF.sub.2 CHFBr                                                                           SCH.sub.3 N                                   I-146           H     OCF.sub.2 CHFCF.sub.3                                                                     SCH.sub.3 N                                   I-147           H     OCH(CH.sub.3).sub.2                                                                       OCH.sub.3 N                                   I-151           H     OCH(CH.sub.3).sub.2                                                                       SCH.sub.3 N                                   I-152           H     OCH(CH.sub.3)CH.sub.2 CH.sub.3                                                            OCH.sub.3 N                                   I-153           H     OCH.sub.2 CF.sub.3                                                                        OCF.sub.2 CHF.sub.2                                                                      N                                   I-154           H     OCH.sub.2 CF.sub.3                                                                        OCH.sub.3 N                                   I-155           H     OCH.sub.2 CHF.sub.2                                                                       OCH.sub.3 N                                   I-156           H     OCH.sub.3  OC.sub.2 H.sub.5                                                                         N                                   I-157           H     OCH.sub.3  OCF.sub.2 CHF.sub.2                                                                      N                                   I-161           H     OCH.sub.3  OCF.sub.2 CHFBr                                                                          N                                   I-162           H     OCH.sub.3  OCF.sub.2 CHFCF.sub.3                                                                    N                                   I-163           H     OCH.sub.3  OCF.sub.2 CHFCl                                                                          N                                   I-164           H     OCH.sub.3  OCH.sub.3 N                                   I-165           H     OCH.sub.3  OCHF.sub.2                                                                               N                                   I-166           H     OCH.sub.3  SCH(CH.sub.3).sub.2                                                                      N                                   I-167           H     OCH.sub.3  SCH.sub.3 N                                   I-168           H     OCH.sub.3  SCHF.sub.2                                                                               N                                   ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                         No.  A          R.sup.1                                                                               X.sup.1    X.sup.2  Z                                   ______________________________________                                         I-171                                                                               In compounds                                                                              CH3    CF.sub.3   OCH.sub.3                                                                               CH                                  I-172                                                                               No. I-171- CH3    CF.sub.3   OCHF.sub.2                                                                              CH                                  I-173                                                                               No. I-338, CH3    CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                               CH                                  I-174                                                                               the group A is                                                                            CH3    CH(OCH.sub.3).sub.2                                                                       CH.sub.3 CH                                  I-175                                                                               A-1(R.sup.2 = R.sup.3 =                                                                   CH3    CH.sub.2 F OCH.sub.3                                                                               CH                                  I-176                                                                               CH.sub.3)  CH3    CH.sub.2 F OCHF.sub.2                                                                              CH                                  I-177           CH3    CH.sub.2 OCH.sub.3                                                                        CH.sub.3 CH                                  I-181           CH3    CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                                                               CH                                  I-182           CH3    CH.sub.2 OCH.sub.3                                                                        OCHF.sub.2                                                                              CH                                  I-183           CH3    CH.sub.3   CF.sub.3 CH                                  I-184           CH3    CH.sub.3   CH.sub.3 CH                                  I-185           CH3    CH.sub.3   Cl       CH                                  I-186           CH.sub.3                                                                              CH.sub.3   F        CH                                  I-187           CH.sub.3                                                                              CH.sub.3   H        CH                                  I-191           CH.sub.3                                                                              CH.sub.3   OC.sub.2 H.sub.5                                                                        CH                                  I-192           CH.sub.3                                                                              CH.sub.3   OCF.sub.2 CHF.sub.2                                                                     CH                                  I-193           CH.sub.3                                                                              CH.sub.3   OCF.sub.2 CHFCF.sub.3                                                                   CH                                  I-194           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CF.sub.3                                                                      CH                                  I-195           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CH.sub.2 F                                                                    CH                                  I-196           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CHF.sub.2                                                                     CH                                  I-197           CH.sub.3                                                                              CH.sub.3   OCH.sub.3                                                                               CH                                  I-201           CH.sub.3                                                                              CH.sub.3   OCHF.sub.2                                                                              CH                                  I-202           CH.sub.3                                                                              CH.sub.3   SCH.sub.3                                                                               CH                                  I-203           CH.sub.3                                                                              CHF.sub.2  CH.sub.3 CH                                  I-204           CH.sub.3                                                                              Cl         Cl       CH                                  I-205           CH.sub.3                                                                              Cl         H        CH                                  I-206           CH.sub.3                                                                              Cl         N(CH.sub.3).sub.2                                                                       CH                                  I-207           CH.sub.3                                                                              Cl         NH.sub.2 CH                                  I-211           CH.sub.3                                                                              Cl         OC.sub.2 H.sub.5                                                                        CH                                  I-212           CH.sub.3                                                                              Cl         OCF.sub.2 CHF.sub.2                                                                     CH                                  I-213           CH.sub.3                                                                              Cl         OCF.sub.2 CHFCl                                                                         CH                                  I-214           CH.sub.3                                                                              Cl         OCH.sub.3                                                                               CH                                  I-215           CH.sub.3                                                                              Cl         OCHF.sub.2                                                                              CH                                  I-216           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         OCF.sub.2 CHF.sub.2                                                                     CH                                  I-217           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         OCH.sub.3                                                                               CH                                  I-221           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         OCHF.sub.2                                                                              CH                                  I-222           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         SCHF.sub.2                                                                              CH                                  I-223           CH.sub.3                                                                              N(CH.sub.3)C.sub.2 H.sub.5                                                                OCHF.sub.2                                                                              CH                                  I-224           CH.sub.3                                                                              N(CH.sub.3)OCH.sub.3                                                                      OCHF.sub.2                                                                              CH                                  I-225           CH.sub.3                                                                              NH.sub.2   OCH.sub.3                                                                               CH                                  I-226           CH.sub.3                                                                              NHCH.sub.3 OCH.sub.3                                                                               CH                                  I-227           CH.sub.3                                                                              NHCH.sub.3 OCHF.sub.2                                                                              CH                                  I-231           CH.sub.3                                                                              OC.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.5                                                                        CH                                  I-232           CH.sub.3                                                                              OCF.sub.2 CHF.sub.2                                                                       SCH.sub.3                                                                               CH                                  I-233           CH.sub.3                                                                              OCH(CH.sub.3).sub.2                                                                       OCHF.sub.2                                                                              CH                                  I-234           CH.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                               CH                                  I-235           CH.sub.3                                                                              OCH.sub.2 CH.sub.2 F                                                                      OCH.sub.3                                                                               CH                                  I-236           CH.sub.3                                                                              OCH.sub.2 CHF.sub.2                                                                       OCH.sub.3                                                                               CH                                  I-237           CH.sub.3                                                                              OCH.sub.3  OC.sub.2 H.sub.5                                                                        CH                                  I-241           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHF.sub.2                                                                     CH                                  I-242           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHFCF.sub.3                                                                   CH                                  I-243           CH.sub.3                                                                              OCH.sub.3  OCH(CH.sub.3).sub.2                                                                     CH                                  I-244           CH.sub.3                                                                              OCH.sub.3  OCH.sub.3                                                                               CH                                  I-245           CH.sub.3                                                                              OCH.sub.3  SCH.sub.3                                                                               CH                                  I-246           CH.sub.3                                                                              OCH.sub.3  SCHF.sub.2                                                                              CH                                  I-247           CH.sub.3                                                                              OCHF.sub.2 OCH.sub.2 CF.sub.3                                                                      CH                                  I-251           CH.sub.3                                                                              OCHF.sub.2 OCH.sub.2 CH.sub.3                                                                      CH                                  I-252           CH.sub.3                                                                              OCHF.sub.2 OCH.sub.3                                                                               CH                                  I-253           CH.sub.3                                                                              OCHF.sub.2 OCHF.sub.2                                                                              CH                                  I-254           CH.sub.3                                                                              OCHF.sub.2 SCH.sub.3                                                                               CH                                  I-255           CH.sub.3                                                                              C.sub.2 H.sub.5                                                                           OCH.sub.3                                                                               N                                   I-256           CH.sub.3                                                                              C.sub.2 H.sub.5                                                                           SCH.sub.3                                                                               N                                   I-257           CH.sub.3                                                                              CF.sub.3   OCH.sub.3                                                                               N                                   I-261           CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        CH.sub.3 N                                   I-262           CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        Cl       N                                   I-263           CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                               N                                   I-264           CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        SCH.sub.3                                                                               N                                   I-265           CH.sub.3                                                                              CH.sub.2 CF.sub.3                                                                         CH.sub.3 N                                   I-266           CH.sub.3                                                                              CH.sub.2 F CH.sub.3 N                                   I-267           CH.sub.3                                                                              CH.sub.2 F OCH.sub.3                                                                               N                                   I-271           CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                        CH.sub.3 N                                   I-272           CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                                                               N                                   I-273           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        CH.sub.3 N                                   I-274           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        Cl       N                                   I-275           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        OC.sub.2 H.sub.5                                                                        N                                   I-276           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        OCH.sub.3                                                                               N                                   I-277           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        SCH.sub.3                                                                               N                                   I-281           CH.sub.3                                                                              CH.sub.3   CF.sub.3 N                                   I-282           CH.sub.3                                                                              CH.sub.3   CH.sub.3 N                                   I-283           CH.sub.3                                                                              CH.sub.3   Cl       N                                   I-284           CH.sub.3                                                                              CH.sub.3   F        N                                   I-285           CH.sub.3                                                                              CH.sub.3   H        N                                   I-286           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CF.sub.3                                                                      N                                   I-287           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CH.sub.2 F                                                                    N                                   I-291           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CHF.sub.2                                                                     N                                   I-292           CH.sub.3                                                                              CH.sub.3   OCH.sub.3                                                                               N                                   I-293           CH.sub.3                                                                              CH.sub.3   SCH.sub.3                                                                               N                                   I-294           CH.sub.3                                                                              CH.sub.3   SCHF.sub.2                                                                              N                                   I-295           CH.sub.3                                                                              CHF.sub.2  CH.sub.3 N                                   I-296           CH.sub.3                                                                              CHF.sub.2  OCH.sub.3                                                                               N                                   I-297           CH.sub.3                                                                              Cl         Cl       N                                   I-301           CH.sub.3                                                                              Cl         OCH(CH.sub.3).sub.2                                                                     N                                   I-302           CH.sub.3                                                                              Cl         OCH.sub.2 CF.sub.3                                                                      N                                   I-303           CH.sub.3                                                                              Cl         OCH.sub.3                                                                               N                                   I-304           CH.sub.3                                                                              Cl         SCH.sub.3                                                                               N                                   I-305           CH.sub.3                                                                              F          OCH.sub.3                                                                               N                                   I-306           CH.sub.3                                                                              H          NH(CH.sub.3)                                                                            N                                   I-307           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         OCH.sub.3                                                                               N                                   I-311           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         SCHF.sub.2                                                                              N                                   I-312           CH.sub.3                                                                              NHCH.sub.3 OCH.sub.3                                                                               N                                   I-313           CH.sub.3                                                                              OC.sub.2 H.sub.5                                                                          OC2H.sub.5                                                                              N                                   I-314           CH.sub.3                                                                              OCF.sub.2 CHF.sub.2                                                                       SCH.sub.3                                                                               N                                   I-315           CH.sub.3                                                                              OCF.sub.2 CHFBr                                                                           SCH.sub.3                                                                               N                                   I-316           CH.sub.3                                                                              OCF.sub.2 CHFCF.sub.3                                                                     SCH.sub.3                                                                               N                                   I-317           CH.sub.3                                                                              OCH(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                               N                                   I-321           CH.sub.3                                                                              OCH(CH.sub.3).sub.2                                                                       SCH.sub.3                                                                               N                                   I-322           CH.sub.3                                                                              OCH(CH.sub.3)CH2CH.sub.3                                                                  OCH.sub.3                                                                               N                                   I-323           CH.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        OCF.sub.2 CHF.sub.2                                                                     N                                   I-324           CH.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                               N                                   I-325           CH.sub.3                                                                              OCH.sub.2 CHF.sub.2                                                                       OCH.sub.3                                                                               N                                   I-326           CH.sub.3                                                                              OCH.sub.3  O.sub.2 H.sub.5                                                                         N                                   I-327           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHF.sub.2                                                                     N                                   I-331           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHFBr                                                                         N                                   I-332           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHFCF.sub.3                                                                   N                                   I-333           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHFCl                                                                         N                                   I-334           CH.sub.3                                                                              OCH.sub.3  OCF.sub.3                                                                               N                                   I-335           CH.sub.3                                                                              OCH.sub.3  OCHF.sub.2                                                                              N                                   I-336           CH.sub.3                                                                              OCH.sub.3  SCH(CH.sub.3).sub.2                                                                     N                                   I-337           CH.sub.3                                                                              OCH.sub.3  SCH.sub.3                                                                               N                                   I-338           CH.sub.3                                                                              OCH.sub.3  SCHF.sub.2                                                                              N                                   ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                         No.  A             R.sup.1 X.sup.1  X.sup.2                                                                              Z                                    ______________________________________                                         I-341                                                                               In compounds  CH.sub.2 Ph                                                                            CH.sub.3 CH.sub.3                                                                             CH                                   I-342                                                                               No. I-341-            CH.sub.3 Cl    CH                                   I-343                                                                               No. I-357,            CH.sub.3 OCH.sub.3                                                                            CH                                   I-344                                                                               the group A is        Cl       Cl    CH                                   I-345                                                                               A-1(R.sup.2 ═R.sup.3 ═CH.sub.3)                                                              Cl       OCH.sub.3                                                                            CH                                   I-346                      OCH.sub.3                                                                               OCH.sub.3                                                                            CH                                   I-347                      CH.sub.3 CH.sub.3                                                                             N                                    I-351                      CH.sub.3 Cl    N                                    I-352                      CH.sub.3 OCH.sub.3                                                                            N                                    I-353                      Cl       Cl    N                                    I-354                      Cl       OCH.sub.3                                                                            N                                    I-355                      N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                            N                                    I-356                      OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                                                            N                                    I-357                      OCH.sub.3                                                                               OCH.sub.3                                                                            N                                    ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                         No.  A             R.sup.1 X.sup.1  X.sup.2                                                                              Z                                    ______________________________________                                         I-361                                                                               In compounds  COCH.sub.3                                                                             CH.sub.3 CH    CH                                   I-362                                                                               No. I-361-            CH.sub.3 Cl    CH                                   I-363                                                                               No. I-377,            CH.sub.3 OCH.sub.3                                                                            CH                                   I-364                                                                               the group A is        Cl       Cl    CH                                   I-365                                                                               A-1(R.sup.2 ═R.sup.3 ═CH.sub.3)                                                              Cl       OCH.sub.3                                                                            CH                                   I-366                      OCH.sub.3                                                                               OCH.sub.3                                                                            CH                                   I-367                      CH.sub.3 CH.sub.3                                                                             N                                    I-371                      CH.sub.3 Cl    N                                    I-372                      CH.sub.3 OCH.sub.3                                                                            N                                    I-373                      Cl       Cl    N                                    I-374                      Cl       OCH.sub.3                                                                            N                                    I-375                      N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                            N                                    I-376                      OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                                                            N                                    I-377                      OCH.sub.3                                                                               OCH.sub.3                                                                            N                                    ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                         No.  A            R.sup.1  X.sup.1  X.sup.2                                                                              Z                                    ______________________________________                                         I-381                                                                               In compounds SO.sub.2 CH.sub.3                                                                       CH.sub.3 CH.sub.3                                                                             CH                                   I-382                                                                               No. I-381-            CH.sub.3 Cl    CH                                   I-383                                                                               No. I-397,            CH.sub.3 OCH.sub.3                                                                            CH                                   I-384                                                                               the group A is        Cl       Cl    CH                                   I-385                                                                               A-1(R.sup.2 ═R.sup.3 ═CH.sub.3)                                                     Cl       OCH.sub.3                                                                               CH                                         I-386                      OCH.sub.3                                                                               OCH.sub.3                                                                            CH                                   I-387                      CH.sub.3 CH.sub.3                                                                             N                                    I-391                      CH.sub.3 Cl    N                                    I-392                      CH.sub.3 OCH.sub.3                                                                            N                                    I-393                      Cl       Cl    N                                    I-394                      Cl       OCH.sub.3                                                                            N                                    I-395                      N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                            N                                    I-396                      OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                                                            N                                    I-397                      OCH.sub.3                                                                               OCH.sub.3                                                                            N                                    ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                         No.  A          R.sup.1                                                                               X.sup.1    X.sup.2  Z                                   ______________________________________                                         I-401                                                                               In compounds                                                                              CH.sub.3                                                                              CF.sub.3   OCH.sub.3                                                                               CH                                  I-402                                                                               No. I-401- CH.sub.3                                                                              CF.sub.3   OCHF.sub.2                                                                              CH                                  I-403                                                                               No. I-568, CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                               CH                                  I-404                                                                               the group A is                                                                            CH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                       CH.sub.3 CH                                  I-405                                                                               A-5        CH.sub.3                                                                              CH.sub.2 F OCH.sub.3                                                                               CH                                  I-406           CH.sub.3                                                                              CH.sub.2 F OCHF.sub.2                                                                              CH                                  I-407           CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                        CH.sub.3 CH                                  I-411           CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                                                               CH                                  I-412           CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                        OCHF.sub.2                                                                              CH                                  I-413           CH.sub.3                                                                              CH.sub.3   CF.sub.3 CH                                  I-414           CH.sub.3                                                                              CH.sub.3   CH.sub.3 CH                                  I-415           CH.sub.3                                                                              CH.sub.3   Cl       CH                                  I-416           CH.sub.3                                                                              CH.sub.3   F        CH                                  I-417           CH.sub.3                                                                              CH.sub.3   H        CH                                  I-421           CH.sub.3                                                                              CH.sub.3   OC.sub.2 H.sub.5                                                                        CH                                  I-422           CH.sub.3                                                                              CH.sub.3   OCF.sub.2 CHF.sub.2                                                                     CH                                  I-423           CH.sub.3                                                                              CH.sub.3   OCF.sub.2 CHFCF.sub.3                                                                   CH                                  I-424           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CF.sub.3                                                                      CH                                  I-425           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CH.sub.2 F                                                                    CH                                  I-426           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CHF.sub.2                                                                     CH                                  I-427           CH.sub.3                                                                              CH.sub.3   OCH.sub.3                                                                               CH                                  I-431           CH.sub.3                                                                              CH.sub.3   OCHF.sub.2                                                                              CH                                  I-432           CH.sub.3                                                                              CH.sub.3   SCH.sub.3                                                                               CH                                  I-433           CH.sub.3                                                                              CHF.sub.2  CH.sub.3 CH                                  I-434           CH.sub.3                                                                              Cl         Cl       CH                                  I-435           CH.sub.3                                                                              Cl         H        CH                                  I-436           CH.sub.3                                                                              Cl         N(CH.sub.3).sub.2                                                                       CH                                  I-437           CH.sub.3                                                                              Cl         NH.sub.2 CH                                  I-441           CH.sub.3                                                                              Cl         OC.sub.2 H.sub.5                                                                        CH                                  I-442           CH.sub.3                                                                              Cl         OCF.sub.2 CHF.sub.2                                                                     CH                                  I-443           CH.sub.3                                                                              Cl         OCF.sub.2 CHFCl                                                                         CH                                  I-444           CH.sub.3                                                                              Cl         OCH.sub.3                                                                               CH                                  I-445           CH.sub.3                                                                              Cl         OCHF.sub.3                                                                              CH                                  I-446           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         OCF.sub.2 CHF.sub.2                                                                     CH                                  I-447           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         OCH.sub.3                                                                               CH                                  I-451           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         OCHF.sub.2                                                                              CH                                  I-452           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         SCHF.sub.2                                                                              CH                                  I-453           CH.sub.3                                                                              N(CH.sub.3)C.sub.2 H.sub.5                                                                OCHF.sub.2                                                                              CH                                  I-454           CH.sub.3                                                                              N(CH.sub.3)OCH.sub.3                                                                      OCHF.sub.2                                                                              CH                                  I-455           CH.sub.3                                                                              NH.sub.2   OCH.sub.3                                                                               CH                                  I-456           CH.sub.3                                                                              NHCH.sub.3 OCH.sub.3                                                                               CH                                  I-457           CH.sub.3                                                                              NHCH.sub.3 OCHF.sub.2                                                                              CH                                  I-461           CH.sub.3                                                                              OC.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.5                                                                        CH                                  I-462           CH.sub.3                                                                              OCF.sub.2 CHF.sub.2                                                                       SCH.sub.3                                                                               CH                                  I-463           CH.sub.3                                                                              OCH(CH.sub.3).sub.2                                                                       OCHF.sub.2                                                                              CH                                  I-464           CH.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                               CH                                  I-465           CH.sub.3                                                                              OCH.sub.2 CH.sub.2 F                                                                      OCH.sub.3                                                                               CH                                  I-466           CH.sub.3                                                                              OCH.sub.2 CHF.sub.2                                                                       OCH.sub.3                                                                               CH                                  I-467           CH.sub.3                                                                              OCH.sub.3  OC.sub.2 H.sub.5                                                                        CH                                  I-471           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHF.sub.2                                                                     CH                                  I-472           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHFCF.sub.3                                                                   CH                                  I-473           CH.sub.3                                                                              OCH.sub.3  OCH(CH.sub.3).sub.2                                                                     CH                                  I-474           CH.sub.3                                                                              OCH.sub.3  OCH.sub.3                                                                               CH                                  I-475           CH.sub.3                                                                              OCH.sub.3  SCH.sub.3                                                                               CH                                  I-476           CH.sub.3                                                                              OCH.sub.3  SCHF.sub.2                                                                              CH                                  I-477           CH.sub.3                                                                              OCHF.sub.2 OCH.sub.2 CF.sub.3                                                                      CH                                  I-481           CH.sub.3                                                                              OCHF.sub.2 OCH.sub.2 CH.sub.3                                                                      CH                                  I-482           CH.sub.3                                                                              OCHF.sub.2 OCH.sub.3                                                                               CH                                  I-483           CH.sub.3                                                                              OCHF.sub.2 OCHF.sub.2                                                                              CH                                  I-484           CH.sub.3                                                                              OCHF.sub.2 SCH.sub.3                                                                               CH                                  I-485           CH.sub.3                                                                              C.sub.2 H.sub.5                                                                           OCH.sub.3                                                                               N                                   I-486           CH.sub.3                                                                              C.sub.2 H.sub.5                                                                           SCH.sub.3                                                                               N                                   I-487           CH.sub.3                                                                              CF.sub.3   OCH.sub.3                                                                               N                                   I-491           CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        CH.sub.3 N                                   I-492           CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        Cl       N                                   I-493           CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                               N                                   I-494           CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        SCH.sub.3                                                                               N                                   I-495           CH.sub.3                                                                              CH.sub.2 CF.sub.3                                                                         CH.sub.3 N                                   I-496           CH.sub.3                                                                              CH.sub.2 F CH.sub.3 N                                   I-497           CH.sub.3                                                                              CH.sub.2 F OCH.sub.3                                                                               N                                   I-501           CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                        CH.sub.3 N                                   I-502           CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                                                               N                                   I-503           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        CH.sub.3 N                                   I-504           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        Cl       N                                   I-505           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        OC.sub.2 H.sub.5                                                                        N                                   I-506           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        OCH.sub.3                                                                               N                                   I-507           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        SCH.sub.3                                                                               N                                   I-511           CH.sub.3                                                                              CH.sub.3   CF.sub.3 N                                   I-512           CH.sub.3                                                                              CH.sub.3   CH.sub.3 N                                   I-513           CH.sub.3                                                                              CH.sub.3   Cl       N                                   I-514           CH.sub.3                                                                              CH.sub.3   F        N                                   I-515           CH.sub.3                                                                              CH.sub.3   H        N                                   I-516           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CF.sub.3                                                                      N                                   I-517           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CH.sub.2 F                                                                    N                                   I-521           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CHF.sub.2                                                                     N                                   I-522           CH.sub.3                                                                              CH.sub.3   OCH.sub.3                                                                               N                                   I-523           CH.sub.3                                                                              CH.sub.3   SCH.sub.3                                                                               N                                   I-524           CH.sub.3                                                                              CH.sub.3   SCHF.sub.2                                                                              N                                   I-525           CH.sub.3                                                                              CHF.sub.2  CH.sub.3 N                                   I-526           CH.sub.3                                                                              CHF.sub.2  OCH.sub.3                                                                               N                                   I-527           CH.sub.3                                                                              Cl         Cl       N                                   I-531           CH.sub.3                                                                              Cl         OCH(CH.sub.3).sub.2                                                                     N                                   I-532           CH.sub.3                                                                              Cl         OCH.sub.2 CF.sub.3                                                                      N                                   I-533           CH.sub.3                                                                              Cl         OCH.sub.3                                                                               N                                   I-534           CH.sub.3                                                                              Cl         SCH.sub.3                                                                               N                                   I-535           CH.sub.3                                                                              F          OCH.sub.3                                                                               N                                   I-536           CH.sub.3                                                                              H          NH(CH.sub.3)                                                                            N                                   I-537           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         OCH.sub.3                                                                               N                                   I-541           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         SCHF.sub.2                                                                              N                                   I-542           CH.sub.3                                                                              NHCH.sub.3 OCH.sub.3                                                                               N                                   I-543           CH.sub.3                                                                              OC.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.5                                                                        N                                   I-544           CH.sub.3                                                                              OCF.sub.2 CHF.sub.2                                                                       SCH.sub.3                                                                               N                                   I-545           CH.sub.3                                                                              OCF.sub.2 CHFBr                                                                           SCH.sub.3                                                                               N                                   I-546           CH.sub.3                                                                              OCF.sub.2 CHFCF.sub.3                                                                     SCH.sub.3                                                                               N                                   I-547           CH.sub.3                                                                              OCH(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                               N                                   I-551           CH.sub.3                                                                              OCH(CH.sub.3).sub.2                                                                       SCH.sub.3                                                                               N                                   I-552           CH.sub.3                                                                              OCH(CH.sub.3)CH.sub.2 CH.sub.3                                                            OCH.sub.3                                                                               N                                   I-553           CH.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        OCF.sub.2 CHF.sub.2                                                                     N                                   I-554           CH.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                               N                                   I-555           CH.sub.3                                                                              OCH.sub.2 CHF.sub.2                                                                       OCH.sub.3                                                                               N                                   I-556           CH.sub.3                                                                              OCH.sub.3  OC.sub.2 H.sub.5                                                                        N                                   I-557           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHF.sub.2                                                                     N                                   I-561           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHFBr                                                                         N                                   I-562           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHFCF.sub.3                                                                   N                                   I-563           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHFCl                                                                         N                                   I-564           CH.sub.3                                                                              OCH.sub.3  OCH.sub.3                                                                               N                                   I-565           CH.sub.3                                                                              OCH.sub.3  OCHF.sub.2                                                                              N                                   I-566           CH.sub.3                                                                              OCH.sub.3  SCH(CH.sub.3).sub.2                                                                     N                                   I-567           CH.sub.3                                                                              OCH.sub.3  SCH.sub.3                                                                               N                                   I-568           CH.sub.3                                                                              OCH.sub.3  SCHF.sub.2                                                                              N                                   ______________________________________                                    

                  TABLE 7                                                          ______________________________________                                         No.  A          R.sup.1                                                                               X.sup.1    X.sup.2  Z                                   ______________________________________                                         I-571                                                                               In compounds                                                                              CH.sub.3                                                                              CF.sub.3   OCH.sub.3                                                                               CH                                  I-572                                                                               No. I-571- CH.sub.3                                                                              CF.sub.3   OCHF.sub.2                                                                              CH                                  I-573                                                                               No. 1-738, CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                               CH                                  I-574                                                                               the group A is                                                                            CH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                       CH.sub.3 CH                                  I-575                                                                               A-2        CH.sub.3                                                                              CH.sub.2 F OCH.sub.3                                                                               CH                                  I-576           CH.sub.3                                                                              CH.sub.2 F OCHF.sub.2                                                                              CH                                  I-577           CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                        CH.sub.3 CH                                  I-581           CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                                                               CH                                  I-582           CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                        OCHF.sub.2                                                                              CH                                  I-583           CH.sub.3                                                                              CH.sub.3   CF.sub.3 CH                                  I-584           CH.sub.3                                                                              CH.sub.3   CH.sub.3 CH                                  I-585           CH.sub.3                                                                              CH.sub.3   Cl       CH                                  I-586           CH.sub.3                                                                              CH.sub.3   F        CH                                  I-587           CH.sub.3                                                                              CH.sub.3   H        CH                                  I-591           CH.sub.3                                                                              CH.sub.3   OC.sub.2 H.sub.5                                                                        CH                                  I-592           CH.sub.3                                                                              CH.sub.3   OCF.sub.2 CHF.sub.2                                                                     CH                                  I-593           CH.sub.3                                                                              CH.sub.3   OCF.sub.2 CHFCF.sub.3                                                                   CH                                  I-594           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CF.sub.3                                                                      CH                                  I-595           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CH.sub.2 F                                                                    CH                                  I-596           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CHF.sub.2                                                                     CH                                  I-597           CH.sub.3                                                                              CH.sub.3   OCH.sub.3                                                                               CH                                  I-601           CH.sub.3                                                                              CH.sub.3   OCHF.sub.2                                                                              CH                                  I-602           CH.sub.3                                                                              CH.sub.3   SCH.sub.3                                                                               CH                                  I-603           CH.sub.3                                                                              CHF.sub.2  CH.sub.3 CH                                  I-604           CH.sub.3                                                                              Cl         Cl       CH                                  I-605           CH.sub.3                                                                              Cl         H        CH                                  I-606           CH.sub.3                                                                              Cl         N(CH.sub.3).sub.2                                                                       CH                                  I-607           CH.sub.3                                                                              Cl         NH.sub.2 CH                                  I-611           CH.sub.3                                                                              Cl         OC.sub.2 H.sub.5                                                                        CH                                  I-612           CH.sub.3                                                                              Cl         OCF.sub.2 CHF.sub.2                                                                     CH                                  I-613           CH.sub.3                                                                              Cl         OCF.sub.2 CHFCl                                                                         CH                                  I-614           CH.sub.3                                                                              Cl         OCH.sub.3                                                                               CH                                  I-615           CH.sub.3                                                                              Cl         OCHF.sub.2                                                                              CH                                  I-616           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         OCF.sub.2 CHF.sub.2                                                                     CH                                  I-617           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         OCH.sub.3                                                                               CH                                  I-621           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         OCHF.sub.2                                                                              CH                                  I-622           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         SCHF.sub.2                                                                              CH                                  I-623           CH.sub.3                                                                              N(CH.sub.3)C.sub.2 H.sub.5                                                                OCHF.sub.2                                                                              CH                                  I-624           CH.sub.3                                                                              N(CH.sub.3)OCH.sub.3                                                                      OCHF.sub.2                                                                              CH                                  I-625           CH.sub.3                                                                              NH.sub.2   OCH.sub.3                                                                               CH                                  I-626           CH.sub.3                                                                              NHCH.sub.3 OCH.sub.3                                                                               CH                                  I-627           CH.sub.3                                                                              NHCH.sub.3 OCHF.sub.2                                                                              CH                                  I-631           CH.sub.3                                                                              OC.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.5                                                                        CH                                  I-632           CH.sub.3                                                                              OCF.sub.2 CHF.sub.2                                                                       SCH.sub.3                                                                               CH                                  I-633           CH.sub.3                                                                              OCH(CH.sub.3).sub.2                                                                       OCHF.sub.2                                                                              CH                                  I-634           CH.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                               CH                                  I-635           CH.sub.3                                                                              OCH.sub.2 CH.sub.2 F                                                                      OCH.sub.3                                                                               CH                                  I-636           CH.sub.3                                                                              OCH.sub.2 CHF.sub.2                                                                       OCH.sub.3                                                                               CH                                  I-637           CH.sub.3                                                                              OCH.sub.3  OC.sub.2 H.sub.5                                                                        CH                                  I-641           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHF.sub.2                                                                     CH                                  I-642           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHFCF.sub.3                                                                   CH                                  I-643           CH.sub.3                                                                              OCH.sub.3  OCH(CH.sub.3).sub.2                                                                     CH                                  I-644           CH.sub.3                                                                              OCH.sub.3  OCH.sub.3                                                                               CH                                  I-645           CH.sub.3                                                                              OCH.sub.3  SCH.sub.3                                                                               CH                                  I-646           CH.sub.3                                                                              OCH.sub.3  SCHF.sub.2                                                                              CH                                  I-647           CH.sub.3                                                                              OCHF.sub.2 OCH.sub.2 CF.sub.3                                                                      CH                                  I-651           CH.sub.3                                                                              OCHF.sub.2 OCH.sub.2 CH.sub.3                                                                      CH                                  I-652           CH.sub.3                                                                              OCHF.sub.2 OCH.sub.2                                                                               CH                                  I-653           CH.sub.3                                                                              OCHF.sub.2 OCHF.sub.2                                                                              CH                                  I-654           CH.sub.3                                                                              OCHF.sub.2 SCH.sub.3                                                                               CH                                  I-655           CH.sub.3                                                                              C.sub.2 H.sub.5                                                                           OCH.sub.3                                                                               N                                   I-656           CH.sub.3                                                                              C.sub.2 H.sub.5                                                                           SCH.sub.3                                                                               N                                   I-657           CH.sub.3                                                                              CF.sub.3   OCH.sub.3                                                                               N                                   I-661           CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        CH.sub.3 N                                   I-662           CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        Cl       N                                   I-663           CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                               N                                   I-664           CH.sub.3                                                                              CH(CH.sub.3).sub.2                                                                        SCH.sub.3                                                                               N                                   I-665           CH.sub.3                                                                              CH.sub.2 CF.sub.3                                                                         CH.sub.3 N                                   I-666           CH.sub.3                                                                              CH.sub.2 F CH.sub.3 N                                   I-667           CH.sub.3                                                                              CH.sub.2 F OCH.sub.3                                                                               N                                   I-671           CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                        CH.sub.3 N                                   I-672           CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                                                               N                                   I-673           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        CH.sub.3 N                                   I-674           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        Cl       N                                   I-675           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        OC.sub.2 H.sub.5                                                                        N                                   I-676           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        OCH.sub.3                                                                               N                                   I-677           CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                                                        SCH.sub.3                                                                               N                                   I-681           CH.sub.3                                                                              CH.sub.3   CF.sub.3 N                                   I-682           CH.sub.3                                                                              CH.sub.3   CH.sub.3 N                                   I-683           CH.sub.3                                                                              CH.sub.3   Cl       N                                   I-684           CH.sub.3                                                                              CH.sub.3   F        N                                   I-685           CH.sub.3                                                                              CH.sub.3   H        N                                   I-686           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CF.sub.3                                                                      N                                   I-687           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CH.sub.2 F                                                                    N                                   I-691           CH.sub.3                                                                              CH.sub.3   OCH.sub.2 CHF.sub.2                                                                     N                                   I-692           CH.sub.3                                                                              CH.sub.3   OCH.sub.3                                                                               N                                   I-693           CH.sub.3                                                                              CH.sub.3   SCH.sub.3                                                                               N                                   I-694           CH.sub.3                                                                              CH.sub.3   SCHF.sub.2                                                                              N                                   I-695           CH.sub.3                                                                              CHF.sub.3  CH.sub.3 N                                   I-696           CH.sub.3                                                                              CHF.sub.2  OCH.sub.3                                                                               N                                   I-697           CH.sub.3                                                                              Cl         Cl       N                                   I-701           CH.sub.3                                                                              Cl         OCH(CH.sub.3).sub.2                                                                     N                                   I-702           CH.sub.3                                                                              Cl         OCH.sub.2 CF.sub.3                                                                      N                                   I-703           CH.sub.3                                                                              Cl         OCH.sub.3                                                                               N                                   I-704           CH.sub.3                                                                              Cl         SCH.sub.3                                                                               N                                   I-705           CH.sub.3                                                                              F          OCH.sub.3                                                                               N                                   I-706           CH.sub.3                                                                              H          NH(CH.sub.3)                                                                            N                                   I-707           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         OCH.sub.3                                                                               N                                   I-711           CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                         SCHF.sub.2                                                                              N                                   I-712           CH.sub.3                                                                              NHCH.sub.3 OCH.sub.3                                                                               N                                   I-713           CH.sub.3                                                                              OC.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.5                                                                        N                                   I-714           CH.sub.3                                                                              OCF.sub.2 CHF.sub.2                                                                       SCH.sub.3                                                                               N                                   I-715           CH.sub.3                                                                              OCF.sub.2 CHFBr                                                                           SCH.sub.3                                                                               N                                   I-716           CH.sub.3                                                                              OCF.sub.2 CHFCF.sub.3                                                                     SCH.sub.3                                                                               N                                   I-717           CH.sub.3                                                                              OCH(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                               N                                   I-721           CH.sub.3                                                                              OCH(CH.sub.3).sub.2                                                                       SCH.sub.3                                                                               N                                   I-722           CH.sub.3                                                                              OCH(CH.sub.3)CH.sub.2 CH.sub.3                                                            OCH.sub.3                                                                               N                                   I-723           CH.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        OCF.sub.2 CHF.sub.2                                                                     N                                   I-724           CH.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                        OCH.sub.3                                                                               N                                   I-725           CH.sub.3                                                                              OCH.sub.2 CHF.sub.2                                                                       OCH.sub.3                                                                               N                                   I-726           CH.sub.3                                                                              OCH.sub.3  OC.sub.2 H.sub.5                                                                        N                                   I-727           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHF.sub.2                                                                     N                                   I-731           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHFBr                                                                         N                                   I-732           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHFCF.sub.3                                                                   N                                   I-733           CH.sub.3                                                                              OCH.sub.3  OCF.sub.2 CHFCl                                                                         N                                   I-734           CH.sub.3                                                                              OCH.sub.3  OCH.sub.3                                                                               N                                   I-735           CH.sub.3                                                                              OCH.sub.3  OCHF.sub.2                                                                              N                                   I-736           CH.sub.3                                                                              OCH.sub.3  SCH(CH.sub.3).sub.2                                                                     N                                   I-737           CH.sub.3                                                                              OCH.sub.3  SCH.sub.3                                                                               N                                   I-738           CH.sub.3                                                                              OCH.sub.3  SCHF.sub.2                                                                              N                                   ______________________________________                                    

                  TABLE 8                                                          ______________________________________                                         No.   A           R.sup.1 X.sup.1  X.sup.2                                                                               Z                                    ______________________________________                                         I-741 In compounds                                                                               CH.sub.3                                                                               CH.sub.3 CH.sub.3                                                                              CH                                   I-742 No. I-741-          CH.sub.3 Cl     CH                                   I-743 No. I-757,          CH.sub.3 OCH.sub.3                                                                             CH                                   I-744 the group A is      Cl       Cl     CH                                   I-745 A-3                 Cl       OCH.sub.3                                                                             CH                                   I-746                     OCH.sub.3                                                                               OCH.sub.3                                                                             CH                                   I-747                     CH.sub.3 CH.sub.3                                                                              N                                    I-751                     CH.sub.3 Cl     N                                    I-752                     CH.sub.3 OCH.sub.3                                                                             N                                    I-753                     Cl       Cl     N                                    I-754                     Cl       OCH.sub.3                                                                             N                                    I-755                     N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                             N                                    I-756                     OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                                                             N                                    I-757                     OCH.sub.3                                                                               OCH.sub.3                                                                             N                                    ______________________________________                                    

                  TABLE 9                                                          ______________________________________                                         No.    A           R.sup.1                                                                               X.sup.1  X.sup.2                                                                               Z                                    ______________________________________                                         I-761  In compounds                                                                               H      CH.sub.3 CH.sub.3                                                                              CH                                   I-762  No. I-761-         CH.sub.3 Cl     CH                                   I-763  No. I-777,         CH.sub.3 OCH.sub.3                                                                             CH                                   I-764  the group A is     Cl       Cl     CH                                   I-765  A-4(R.sup.4 ═H)                                                                               Cl       OCH.sub.3                                                                             CH                                   I-766                     OCH.sub.3                                                                               OCH.sub.3                                                                             CH                                   I-767                     CH.sub.3 CH.sub.3                                                                              N                                    I-771                     CH.sub.3 Cl     N                                    I-772                     CH.sub.3 OCH.sub.3                                                                             N                                    I-773                     Cl       Cl     N                                    I-774                     Cl       OCH.sub.3                                                                             N                                    I-775                     N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                             N                                    I-776                     OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                                                             N                                    I-777                     OCH.sub.3                                                                               OCH.sub.3                                                                             N                                    ______________________________________                                    

The N-(substituted amino)imide derivative of the above formula (I-a) can be synthesized by reacting an aminoazine derivative of the formula (V) with a halogenosulfonyl isocyanate of the formula (VI) to form an (azinylureylene)sulfonylhalide of the formula (III), followed by reacting it with an N-aminoimide derivative of the formula (II-a) without preferably isolating the intermediate, according to the following reaction formula. ##STR8##

The N-(substituted amino)imide derivative of the above formula (I-b1) can also be synthesized by reacting a compound or the formula (I-b2) with a compound of the formula (IV) in a presence of a base to replace the hydrogen atom on N-amino group with R¹ b according to the following reaction formula: ##STR9##

The compounds of the above formula (I-a) can be prepared by the following steps.

In the first step, an aminoazine derivative of the formula (V) is allowed to react with a halogenosulfonyl isocyanate of the formula (VI) in an inert organic solvent or diluent to form an (azinylureylene)sulfonylhalide of the formula (III), followed by reacting it with an N-aminoimide derivative of the formula (II-a) without preferably isolating the intermediate, according to the following reaction formula. If desired, the resultant compound of the formula (I-a) is allowed to react with alkali metal hydroxide or quaternary ammonium base to form a salt thereof.

The above reaction steps are preferred to carry out at a temperature in a range of from -78° C. to boiling point of the solvent and preferably from 0° C. to 40° C. in an inert organic solvent, for example, hydrocarbons such as benzene, toluene, xylene or cyclohexane, etc., chlorinated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride or chlorobenzene, ethers such as diethyl ether, dimethoxyethane, diethyleneglycol dimethyl ether, tetrahydrofuran, dioxane, and aprotic polar solvent such as acetonitrile or nitromethane.

In these reactions, it is preferred to use an organic tertiary amine, preferably pyridine or triethylamine, or an inorganic base such as carbonates of alkali metal as an acid acceptor.

If necessary, the compound of the formula (II-a) may be used in an excess amount so as to simultaneously react as an auxiliary base.

The reaction for replacing hydrogen atom of N-amino group on the imide group of the compound represented by the formula (I-b2) with the group R¹ b is carried out at a temperature in a range of from 0° C. to the boiling point of the solvent in the presence of an inorganic base such as sodium hydroxide or potassium carbonate in a solvent such as dioxane or dimethylacetamide. As a substitution reagent, a reagent which form the group R¹ b as an electrophilic cation can be used.

Examples of alkylating agent include dimethyl sulfate, methyl iodide, ethyl iodide, ethyl bromide and benzyl bromide, etc. Examples of acylating agent include acetyl chloride, propionyl chloride, butyryl chloride, acetic acid anhydride and propionic acid anhydride, etc. Examples of sulfonylating agent include methanesulfonyl chloride, ethanesulfonyl chloride and propanesulfonyl chloride, etc.

After completion of the reaction, the reaction mixture is added to an aqueous solution of diluted hydrochloric acid and the precipitate thus formed is collected by filtration. The precipitate is dried in air and then purified by column chromatography or by washing technique, whereby the N-(substituted amino)imide derivative of the formula (I-1b) can be obtained.

The compound of the formula (I) is possible to replace a hydrogen atom on the nitrogen atom of ureylene group with a suitable cation to form a salt. Examples of the salt generally include metal salts, particularly alkali metal salts and alkaline earth metal salts, and if necessary, ammonium salts and organic amine salts. The salts can be produced preferably at a temperature in a range of from 20° to 100° C. in a solvent such as water, alcohol or acetone. Preferred examples of the base for producing the salt of the compound (I) include alkali metal carbonates, ammonia and ethanolamine.

The starting material of the formula (V) can be synthesized by cyclization of a suitable guanidine derivative with a substituted 1,3-diketone. (The Chemistry of Heterocyclic Compounds., Vol.XVI (1962) and Supplement I (1970)).

The above compound can also be synthesized from an N-cyanoamidine derivative or an N-cyanoimidate derivative. (Refer to Journal of Organic Chemistry (J. Org. Chem.) 28., 1812-1821 (1963)).

Further, the above compound can be synthesized from cyanuric chloride. (For example, L. Rapoport: "The Chemistry of Heterocyclic Compounds", "s-triazines and Derivatives" (1959)).

Synthesis of the compound of the formula (II-a) can be carried out as follows. That is, the compound can be synthesized by reacting a 1,2-dicarboxylic acid of the formula (VIII) or mono- or diester thereof or, preferably, a 1,2-dicarboxylic acid anhydride of the formula (VII) with a hydrazine derivative of the formula (IX) in acetonitrile, lower alcohol, hydrochloric acid containing lower alcohol, or acetic acid, according to the following reaction formula. ##STR10## wherein R⁵ is hydrogen atom or C₁ -C₄ alkyl group and R⁶ is C₁ -C₄ alkyl group.

Specific examples of compounds represented by the formula (II-a) used as the above described intermediates are shown in Table 10.

                  TABLE 10                                                         ______________________________________                                         Compound                                                                       No.           A               R.sup.1                                          ______________________________________                                         II-1          A-1(R.sup.2 ═R.sup.3 ═CH.sup.3)                                                        H                                                II-2          A-1(R.sup.2 ═R.sup.3 ═CH.sup.3)                                                        CH.sup.3                                         II-3          A-1(R.sup.2 ═R.sup.3 ═CH.sup.3)                                                        CH.sub.2 Ph                                      II-4          A-2             H                                                II-5          A-2             CH.sup.3                                         II-6          A-2             CH.sub.2 Ph                                      II-7          A-3             H                                                II-8          A-3             CH.sup.3                                         II-9          A-3             CH.sub.2 Ph                                      II-10         A-4(R.sup.4 ═H)                                                                            H                                                II-11         A-4(R.sup.4 ═H)                                                                            CH.sup.3                                         II-12         A-4(R.sup.4 ═H)                                                                            CH.sub.2 Ph                                      ______________________________________                                    

The N-(substituted amino)imide derivative of the above formula (I) according to the present invention which is novel compound exhibits a certain herbicidal effect in a low dosage, and has a selectivity between crops and weeds. Accordingly, a herbicidal composition comprising this compound as an active ingredient is suitable, e.g., for controlling monocotyledonous and dicotyledonous weed in important crops, such as wheat, rice, corn, soybean, cotton, beet, potato and tomato, before or after germination.

Examples of dicotyledonous weeds which can be prevented by the herbicidal composition of the present invention include weeds belonging to Amaranthus, Bidens, Stellaria, Abutlion, Convolvulus, Matricaria, Galium, Lindernia, and the like.

Examples of monocotyledonous weeds include weeds belonging to Echinochloa, Setaria, Digitaria, Arena, Cyperus, Alisma, Monochoria, and the like.

The herbicidal composition according to the present invention may be applied in areas such as farming areas, inclusive of farms, paddy fields and orchards, as well as non-farming areas, inclusive of grounds and industrial sites.

The compound of the present invention can be utilized as is, but it is generally used in various forms of preparations, such as dust, wettable powder, granule, emulsion, etc., together with a preparation adjuvant.

In this case, a preparation is prepared so that one or more compounds of the present invention are contained in an amount of 0.1 to 95% by weight, preferably 0.5 to 90% by weight, and particularly 2 to 70% by weight.

Examples of carriers, diluents, and surfactant, which can be used as the preparation adjuvant, include talc, kaolin, bentonite, diatom earth, white carbon, clay, and the like. As liquid diluents, water, xylene, toluene, chlorobenzene, cyclohexane, cyclohexanone, dimethylsulfoxide, dimethylformamide, alcohols, and the like can be exemplified.

Surfactants are preferably used depending upon their effects. Examples of emulsifiers are polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monolaurate, etc.; examples of dispersants are lignin sulfonates, dibutylnaphthalene sulfonate, etc.; and examples of wetting agents are alkylsulfonates, alkylphenyl sulfonates, etc.

The above-mentioned preparation can be roughly divided into one which is used as is and one which is used by diluting with a diluent such as water. In the latter case, the concentration of the compound of the present invention preferably ranges from 0.001 to 1.0%.

The amount of the compound of the present invention used is in a range of from 0.01 kg to 10 kg, preferably 0.05 kg to 5 kg, per 1 ha.

Since the concentration and the amount used vary with the form of preparation, the period of usage, the manners of usage, the sites of the usage, the intended crops, and other factors, these values can, of course, be changed in spite of the above ranges. Moreover, the compound of the present invention can be used in combination with other active ingredients, such as fungicides, bactericides, miticides and herbicides.

EXAMPLES

The present invention will now be described in detail by referring to Synthesis Examples of the N-(substituted amino)imide derivatives represented by the formula (I), Preparation Examples and Test Example. The present invention is not limited to the following Synthesis Examples, Preparation examples and Test Example unless departing from the scope of the present invention. Synthesis Example 1

Synthesis of N-(4,6-dimethoxy-2-pyrimidinyl)-N'-{ (2,3-dimethylmaleimido)amino!sulfonyl}urea (I-74)

To a solution of chlorosulfonylisocyanate (0.94 g: 6.5×1.02 mM) dissolved in 10 ml of dichloromethane at -70° C. was added dropwise 20 ml of a solution of 2-amino-4,6-dimethoxypyrimidine (1.0 g, 6.5 mM) in dichloromethane. Then, the temperature of the reaction system was controlled over 1 hour so as to be near 0° C. After cooling again to -70° C., a solution of N-2,3-dimethylmaleimide (1.82 g; 6.5×22 mM) in 10 ml of dichloromethane was added dropwise.

The mixture was then stirred over a night while the temperature was elevated to room temperature. Thereafter, the solvent in the reaction mixture was distilled at room temperature, and water was added to the resultant residue. The precipitated solid was filtered off. The resultant product was washed with hot acetonitrile to obtain the target product.

Yield 0.52 g (52%); HPLC purity 99.7% (254 nm); White solid; m.p. 190° C. (decomposition)

IR(KBr cm⁻¹): 3292 1746 1704 1614 1578 1500 1455 1365 1200 1173

¹ H-NMR(60 MHz; d₆ -DMSO, δ)=1.85(6H,s, maleimide ring CH₃×2) 3.76(6H,s, pyrimidine ring OCH₃×2) 5.8(1H,s, pyrimidine ring H) 10.5(1H,s,NH) 11.0(1H,s,NH) 12.3(1H,s,NH)

Synthesis Example 2

Synthesis of N-(4,6-dimethoxy-2-pyrimidinyl)-N'-{ (2,3-dimethylmaleimido)(methyl)amino!sulfonyl}urea (I-244)

To a solution of chlorosulfonylisocyanate (0.48 g: 3.2×1.05 mM) dissolved in 10 ml of dried dichloromethane at -70° C. was added dropwise 20 ml of a solution of N-(methylamino)-2,3-dimethylmaleimide (II-2)(0.5 g, 3.2 mM) in dichloromethane, followed by adding dropwise 10 ml of a solution of triethylamine (0.42 g, 3.2×1.1mM). The reaction mixture was stirred for 20 hours while the temperature was raised to room temperature. Thereafter, the solvent in the reaction mixture was distilled, and water was added to the resultant residue. The precipitated solid was filtered off. The resultant solid was washed with a small amount of hot ethyl acetate and purified by chromatography.

Yield 0.737 g, (55%); purity 98.4%(254 nm); white solid; m.p. 169°-171° C.;

IR (KBr cm⁻¹): 1742 1710 1610 1582 1506 1456 1378 1360 1222 1162;

¹ H-NMR (60 MHz; CDCl₃, δ): 1.97(6H,s, maleimide ring CH₃×2) 3.49(3H,s, N--CH₃) 3.86(6H,s, pyrimidine ring OCH₃ ×2) 5.78(1H,s, pyrimidine ring H) 7.63(1H,bs,NH) 12.6(1H,bs, NH).

Synthesis Example 3

Synthesis of N{ (benzyl)(2,3-dimethlmaleimido)-amino!sulfonyl}-N'-(4,6-dimethoxy-2-pyrimidinyl)urea (I-346)

The target compound was synthesized by ureylenesulfonylation of N-(benzylamino)-2,3-dimethylmaleimide (II-3) synthesized according to the below-mentioned Reference Synthesis Example 2, by the same manner as in Synthesis Example 1.

Yield 0.98 g (74.2%); HPLC purity 95.4%; white solid; m.p. 171°-173° C.

IR (KBr cm-1): 1743 1713 1611 1584 1461 1362

¹ H-NMR (60 MHz; CDCl₃, δ): 1.8(6H,s, maleimide ring CH₃ ×2) 3.8(6H,s, pyrimidine ring OCH₃ ×2) 5.05(2H,s, N-CH₂) 5.66(1H,s, pyrimidine ring H) 7.1-7.3(5H,m, benzene ring H) 7.63(1H,br,NH) 12.5(1H,br,NH).

Synthesis Example 4

Synthesis of N-(4,6-dimethoxy-2-pyrimidinyl)-N'-{ (acetyl) (2,3-dimethylmaleimido)amino!sulfonyl}urea (I-366)

N-(4,6-dimethoxypyrimidin-2-yl)-N'-{ (2,3-dimethylmaleimido)amino!sulfonyl}urea (I-74)(0.78 g, 1.95 mmol) synthesized according to synthesis Example 1 was dissolved in 20 ml of dried dimethylformamide. To the solution was added under cooling with ice-water 60% sodium hydride (0.078 g, 1.95 mmol). After conclusion of foaming, acetic acid anhydride (0.2 g, 1.95 mmol) was added and stirred at room temperature for 20 hours. The reaction mixture was then poured into ice-water, and the solid precipitate was filtered, washed with water and dried.

Yield 0.48 g (56.6%); HPLC purity (254 nm)98.4%; white solid; m.p. 167°-168° C. (decomposition);

IR (KBr cm⁻¹): 3272 2932 1748 1718 1620 1584 1512 1454 1378 1228 1174;

¹ H-NMR (60 MHz: d₆ -DMSO, δ): 1.93(6H,s, maleimide ring CH₃×2) 2.5(3H,s,COCH₃) 3.73(1H,s,NH) 3.81(6H,s, pyrimidine ring OCH₃ ×2) 10.7(1H,s,NH);

MS DI!: m/z 181(dimethylimide --NCOCH₃,2) 43(100)

Synthesis Example 5

Synthesis of N-(4,6-dimethoxy-2-pyrimidinyl)-N'-{ (2,3-dimethylmaleimido)(methylsulfonyl)amino!-sulfonyl}urea (I-386)

N-(4,6-dimethoxypyrimidin-2-yl)-N'-{ (2,3-dimethylmaleimido)amino!sulfonyl}urea (I-74)(0.32 g, 0.81 mM) synthesized according to synthesis Example 1 was dissolved in 20 ml of dried dimethylformamide. To the solution was added under cooling with ice-water 60% sodium hydride (0.0324 g, 0.81 mM). After conclusion of foaming, methylsulfonyl chloride (0.093 g, 0.81 mM) was added and stirred at room temperature for 17 hours. The reaction mixture was then poured into water, and extracted with ethyl acetate. The resultant organic layer was washed with diluted hydrochloric acid and saturated saline solution. After ethyl acetate was distilled away, the product was purified by chromatography.

Yield 0.044 g (11.4%); HPLC purity (254 nm) 95.0%; white solid; m.p. 160°-162° C. (decomposition)

IR (KBr cm): 1770 1635 1380 1200;

¹ H-NMR (60 MHz; CDCl₃, δ): 1.98(6H,s, maleimide ring CH₃ ×2) 3.45(3H,s, SO₂ CH₃) 3.85(6H,S, pyrimidine ring OCH₃ ×2) 5.68(1H,s, pyrimidine ring H) 7.38(1H,br, NH) the others are indistinct.

Synthesis Example 6

Synthesis of N-(4,6-dimethoxy-2-pyrimidinyl)-N'-{ (maleimido)(methyl)amino!sulfonyl}urea (I-474)

N-(4,6-dimethoxy-2-pyrimidinyl)-N'-{ (exo-3,6-epoxy-1,2,3,6-tetrahydrophthalimido)(methyl)amino!sulfonyl}urea (I-644) (0.4 g, 0.88 mmol) synthesized according to the below-mentioned Synthesis Example 7 was heated at 140° C. for 1 hour in the absence of solvent. After cooling, 20 ml of acetonitrile was added. After stirred, the mixture was filtered to obtain 0.16 g of a solid product. It was dissolved in 5 ml of dimethylformamide and reprecipitated by adding 10 ml of water. The solid precipitate was filtered, washed with water and dried.

Yield 0.048 g (14.1%); HPLC purity (254 nm) 91%; white solid; m.p. 197° C. (decomposition)

IR (KBr cm⁻¹): 1743 1716 1617 1578 1452 1377 1161

¹ H-NMR (60 MHz: d₆ -DMSO, δ): 3.3(3H,S, N--CH₃) 3.73(6H,S, pyrimidine ring OCH₃ ×2) 5.8(1H,S, pyrimidine ring H) 7.0(2H,S, maleimide ring H×2) 10.4(1H,S,NH) 12.3(1H,brs, NH)

LC/MS DI!: m/z 387(M+1)

Synthesis Example 7

Synthesis of N-(4,6-dimethoxy-2-pyrimidinyl)-N'-{ (exo-3,6-epoxy-1,2,3,6-tetrahydrophthalimido)(methyl)-amino!sulfonyl}urea (I-644)

The target compound was synthesized by ureylenesulfonylation of exo-3,6-epoxy-N-(methylamino)-1,2,3,6-tetrahydrophthalimide (II-5) synthesized according to the below-mentioned Reference Synthesis Example 3, by the same manner as in Synthesis Example 1.

Yield 0.55 g (59.1%); HPLC purity (254 nm) 97.4%; white solid; m.p. begin to fuse at 177° C. and decompose at 186° C.;

IR (KBr cm⁻¹): 3262 3022 1797 1746 1614 1575 1455 1368

¹ H-NMR (60 MHz; d₆ -DMSO, δ): 2.8(2H,m, epoxytetrahydrophthalimide ring H) 3.3(3H,s, NCH₃) 3.78(6H,s, pyrimidine ring OCH₃ ×2) 4.78-5.18(2H, epoxytetrahydrophthalimide ring H) 5.84(1H,s, pyrimidine ring H) 10.5(1H,bs,NH) 12.5(1H,bs,NH)

Synthesis Example 8

Synthesis of N-(4,6-dimethoxy-2-pyrimidinyl)-N'-{ (methyl)(cis-5-norbornene-end-2,3-dicarboxyimido)amino!sulfonyl}urea (I-746)

The target compound was synthesized by ureylenesulfonylation of N-(methylamino)-cis-5-norbornene-endo-2,3-dicarboximide (II-8) synthesized according to the below-mentioned Reference Synthesis Example 4, by the same manner as in Synthesis Example 1.

Yield 0.42 g (6.0%); HPLC purity (254 nm) 95.4%; white solid; m.p.170°-175° C. (decomposition at 193° C.)

IR (KBr cm⁻¹): 1743 1611 1455 1362 1197 1173

¹ H-NMR (60 MHz; d₆ -DMSO, δ): 1.46(2H,m, norbornene ring H) 3.06×3.41(7H,m, NCH₃, norbornene ring H×4) 3.76, 3.8(each 3H,s, pyrimidine ring OCH₃ ×2) 5.77-6.1(3H,m, norbornene ring H×2, pyrimidine ring H) 10.46(1H,bs,NH) 12.2(1H,bs,NH)

Synthesis Example 9

Synthesis of N-(4,6-dimethoxy-2-pyrimidinyl)-N'- (phthalimidoamino)sulfonyl!urea (I-766)

The target compound was synthesized by ureylenesulfonylation of N-aminophthalimide according to the same manner as in Synthesis Example 1.

Yield 0.49 g (60%); HPLC (254 nm) purity 99.6%; white solid; m.p. 183°-185° C. (decomposition);

IR (KBr cm⁻¹); 3228 1798 1732 1612 1586 1454 1364 1200

¹ H-NMR (60 MHz; d₆ -DMSO, δ): 3.75(6H,s, pyrimidine ring OCH₃ ×2) 5.83(1H,s, pyrimidine ring H) 7.86(4H,s, benzene ring H) 10.5(1H,s, NH) 11.26(1h,bs,NH) 12.3(1H,bs,NH)

Reference Synthesis Example 1

Synthesis of N-(methylamino)-2,3-dimethylmaleimide (II-2) intermediate for Synthesis Example 2!

2,3-Dimethylmaleic acid anhydride (3.5 g, 28 mM) was suspended in 50 ml of ethyl alcohol. To the dispersion was added methylhydrazine (1.28 g, 27.7 mM). After addition, the mixture was stirred at 70° C. for 3 hours. After ethanol was distilled away, the target compound was separated by chromatography from the reaction mixture.

Yield 0.7 g (16.4%); HPLC purity 97.8 %; light green solid; m.p. 61°-62° C.;

¹ H-NMR (60 MHz; CDCl₃ δ): 1.93(6H,s; CH₃ ×2) 2.66(3H,d,J=5 Hz;NHCH₃) 4.22(1H,bq,J=5 Hz; NH)

Reference Synthesis Example 2

Synthesis of N-(benzylamino)-2,3-dimethylmaleimide (II-3) intermediate for Synthesis Example 3!

The target compound was synthesized by reacting benzylhydrazine with 2,3-dimethylmaleic acid anhydride according to the same manner as in Reference Synthesis Example 1.

Yield 1.28 g (23.3%); HPLC purity 95.8%; light yellow solid; m.p. 95°-97° C.;

IR (KBr cm⁻¹): 3274 1779 1713 1491 1458 1398 1095 753

¹ H-NMR (60 MHz; CDCl₃, δ): 1.9(6H,S: maleimide ring CH₃ ×2) 4.0(2H,bs: NHCH₂) 4.36(1H,bs:NH) 7.06˜7.46(5H,m benzene ring H)

Reference Synthesis Example 3

Synthesis of exo-3,6-epoxy-N-(methylamino)-1,2,3,6-tetrahydrophthalimide (II-5) intermediate for Synthesis Example 7!

Exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic acid anhydride (3.5 g, 21 mM) was dissolved in 50 ml of acetonitrile. To the solution was added dropwise methylhydrazine (0.97 g, 21 mM) in 5 ml of acetonitrile at room temperature. The mixture was refluxed with heat to 70° C. for 4 hours. After cooled, the precipitated solid was filtered off and the filtrate was condensed. The residue was purified with column chromatography on silica gel (elution solvent: ethyl acetate/n-hexane=1/1) to obtain the target compound as white solid.

Yield 0.69 g (16.9%); white solid; m.p. 155° C. (decomposition);

IR (KBr cm⁻¹): 3316 1782 1713 1530 1248 1179 1014 876 717

¹ H-NMR (60 MHz; CDCl₃, δ): 2.62(3H,S, N--CH₃) 2.73(2H,s, epoxytetrahydrophthalimide ring H) 4.23(1H,br, NH) 5.18(2H,s, epoxytetrahydrophthalimide ring H) 6.4(2H,s, epoxytetrahydrophthalimide ring H)

Reference Synthesis Example 4

Synthesis of N-(methylamino)-cis-5-norbornene-endo-2,3-dicarboximide (II-8) intermediate for Synthesis Example 8!

The target compound was synthesized by reacting cis-5-norbornene-endo-2,3-dicarboxylic acid anhydride with methyl hydrazine according to the same manner as in Reference Synthesis Example 3.

Yield 0.93 g (22.7%); white solid; m.p. 126°-130° C.;

IR (KBr cm⁻¹): 3316 3004 1767 1713 1509 1389 1242 1173 1134 726

¹ H-NMR (60 MHz; CDCl₃, δ): 1.47(1H,m, norbornene ring H) 1.74(1H,m, norbornene ring H) 2.53(3H,s, NCH₃) 3.08-3.53(4H,m, norbornene ring H) 4.26(1H,br,NH) 6.03(2H,m, norbornene ring H)

In the above Synthesis Examples and Reference Synthesis Examples symbols in NMR have the following meanings:

s (single), d (doublet), t (triplet), q (quartet), m (multiplet), dd (double doublet), and br (broad).

Formulation Examples and Test Examples will hereinafter be described. It should be borne in mind that the vehicles (diluents), adjuvants, their mixing ratio and effective components can vary in wide ranges respectively. In these examples, all "parts" are by weight. Formulation Example 1 (Wettable Powder)

    ______________________________________                                         Compound (I-386)  50 parts                                                     Salt of ligninsulfonic acid                                                                       5 parts                                                     Salt of alkylsulfonic acid                                                                        3 parts                                                     Diatomaceous earth                                                                               42 parts                                                     ______________________________________                                    

The above ingredients are mixed and ground into a wettable powder. For application, it is diluted with water.

Formulation Example 2 (Emulsion)

    ______________________________________                                         Compound (I-746)    25 parts                                                   Xylene              65 parts                                                   Polyoxyethylene alkylaryl ether                                                                    10 parts                                                   ______________________________________                                    

The above ingredients are mixed intimately into an emulsion. For application, it is diluted with water. Formulation Example 3 (Granule)

    ______________________________________                                         Compound (I-244)                                                                                8 parts                                                       Bentonite       40 parts                                                       Clay            45 parts                                                       Ligninsulfonic acid                                                                             7 parts                                                       ______________________________________                                    

The above ingredients are mixed intimately. After the addition of water, the mixture was kneaded and then formed into granules by an extruding granulator. Test 1 Test on herbicidal activity by foliar application

Herbicidal solutions of each test compound, which had been prepared by dissolving at predetermined concentrations such as wettable powder of the test compound as that described in the above formulation example, and sprayed at a dosage of 1000 g/ha over foliar parts of Amaranthus retroflexus, Bidenes pilosa, Sinapis arvensis, Stellaria media, Cassia obtusifolia, Solanum nigrum, Abutilon theophrasti, Convolvulus arvensis, Matricaria chamomilla, Galium aparine, Veronica hederaeforia, Setaria viridis, Echinochloa frumentaceum, Arena fatua, Digitaria adscendens (which had been allowed to grow individually to 1-2 leaf stage). Fourteen days later after spraying of the test compound, its herbicidal activity was evaluated in accordance with the below-described 3-stage system. The results are summarized in Table II. Growth inhibition rate

1: less than 30%; 2: 30% to less than 70%; 3: 70% or more

                  TABLE II                                                         ______________________________________                                         Compound (I) 1000 g/ha                                                         Feed  74     244    346  366  386  474  644  746  766                          ______________________________________                                         A.r.  3      3      1    3    2    3    2    2    2                            B.p.  2      3      1    2    2    3    2    2    1                            S.a.  3      3      3    3    3    3    3    3    1                            S.m.  1      3      1    1    2    3    1    3    1                            C.f.  1      3      1    3    2    3    1    1    1                            S.n.  3      3      1    3    2    3    1    2    1                            A.t.  3      3      1    2    1    2    1    1    1                            C.a.  3      3      1    3    2    3    1    1    1                            M.c.  3      3      1    1    1    3    1    1    1                            G.a.  2      3      1    3    3    3    1    1    1                            V.h.  2      3      1    2    3    1    1    1    1                            S.v.  1      3      1    1    3    1    1    1    1                            E.f.  1      3      1    1    3    2    1    1    1                            A.f.  1      2      1    1    2    2    1    1    1                            D.a.  1      1      1    1    1    2    1    1    1                            ______________________________________                                          A.r.: Amaranthus retroflexus                                                   B.p.: Bidenes pilosa                                                           S.a.: Sinapis arvensis                                                         S.m.: Stellaria media                                                          C.f.: Cassia obtusifolia                                                       S.n.: Solanum nigrum                                                           A.t.: Abutilon theophrasti                                                     C.a.: Convolvulus arvensis                                                     N.c.: Natricaria chamomilla                                                    G.a.: Galium aparine                                                           V.h.: Veronica hederaeforia                                                    S.v.: Setaria viridis                                                          E.f.: Echinochloa frumentaceum                                                 A.f.: Avens fetua                                                              D.a.: Digitaria adscendens                                                

We claim:
 1. An N-(substituted amino)imide derivative represented by the formula (I): ##STR11## wherein, R¹ is a hydrogen atom, C₁ -C₄ alkyl group, C₇ -C₉ aralkyl group, C₁ -C₄ haloalkyl group, (C₁ -C₄ alkyl)carbonyl group or a (C₁ -C₄ alkyl) sulfonyl group;A represents a structure selected from the group consisting of the following formulas (1), (2), (3) and (4) ##STR12## wherein R² and R³ in the formula (1) are independently a hydrogen atom or a C₁ -C₄ alkyl group, but not R² ═R³ ═H, X¹ and X² are independently a hydrogen atom, a halogen atom, C₁ -C₄ alkyl group, C₁ -C₄ alkoxy group, C₁ -C₄ alkylthio group, C₁ -C₄ haloalkyl group, C₁ -C₄ haloalkoxy group, C₁ -C₄ haloalkylthio group, C₂ -C₄ alkoxyalkyl group, C₂ -C₄ thioalkoxyalkyl group, or NR⁷ R⁸, wherein R⁷ and R⁸ are independently a hydrogen atom, C₁ -C₄ alkyl group or C₁ -C₄ alkoxy group; and Z is a nitrogen atom or CH.
 2. The N-(substituted amino)imide derivative according to claim 1, wherein Z is CH and A is of the formula (1) R² ═R³ =methyl, formula (2), formula (3) or formula (4).
 3. The N-(substituted amino)imide derivative according to claim 1, wherein Z is N, and A is of the formula (1) where R² ═R³ =methyl, formula (2), formula (3) or formula (4).
 4. A process for preparation of an N-(substituted amino)imide derivative represented by the formula (I-a), which comprises reacting an N-aminoimide derivative of the formula (II-a) with an (azinylureylene)sulfonyl halide of the formula (III): ##STR13## wherein Aa is a structure selected from the group consisting of the following formulas (1), (2), (3) and (4) ##STR14## wherein R² and R³ in the formula (1) are independently a hydrogen atom or a C₁ -C₄ alkyl group, but not R²═R³ ═H; X¹ and X² are independently a hydrogen atom, a halogen atom, C₁ -C₄ alkyl group, C₁ -C₄ alkoxy group, C₁ -C₄ alkylthio group, C₁ -C₄ haloalkyl group, C₁ -C₄ haloalkoxy group, C₁ -C₄ haloalkylthio group, C₁ -C₄ alkoxyalkyl group, C₂ -C₄ thioalkoxyalkyl group or NR⁷ R⁸, wherein R⁷ and R⁸ are independently a hydrogen atom, C₁ -C₄ alkyl group or C₁ -C₄ alkoxy group; Z is a nitrogen atom or CH; and Y¹ is a halogen atom.
 5. A process for preparation of an N-(substituted amino) imide derivative represented by the formula (I-b1), which comprises reacting an N-(substituted amino)imide derivative of the formula (I-b2) with a compound represented by the formula (IV) in the presence of a base to replace the hydrogen atom on N-amino group with R¹ b: ##STR15## wherein Aa is a structure selected from the group consisting of the following formulas (1), (2) or (3) ##STR16## wherein R² and R³ in the formula (1) are independently a hydrogen atom or a C₁ -C₄ alkyl group, but not R² ═R³ ═H; X¹ and X² are independently a hydrogen atom, a halogen atom, C₁ -C₄ alkyl group, C₁ -C₄ alkoxy group, C₁ -C₄ alkylthio group, C₁ -C₄ haloalkyl group, C₁ -C₄ haloalkoxy group, C₁ -C₄ haloalkylthio group, C₂ -C₄ alkoxyalkyl group, C₂ -C₄ thioalkoxyalkyl group or NR⁷ R⁸, wherein R⁷ and R⁸ are independently hydrogen atom, C₁ -C₄ alkyl group or C₁ -C₄ alkoxy group; Z is a nitrogen atom or CH; R¹ b is C₁ -C₄ alkyl group, C₇ -C₉ aralkyl group, C₁ -C₄ haloalkyl group, (C₁ -C₄ alkyl)carbonyl group or (C₁ -C₄ alkyl)sulfonyl group; and Y² is a halogen atom or C₁ -C₄ alkyl) carbonyl!oxy group.
 6. A process for preparation of an N-(substituted amino)imide derivative of the formula (I-c1), which comprises pyrolysis of an N-(substituted amino)imide derivative of the formula (i-c2): ##STR17## wherein R¹ c is C₁ -C₄ alkyl group, C₇ -C₉ aralkyl group or C₁ -C₄ haloalkyl group, X¹ and X² are independently a hydrogen atom, a halogen atom, C₁ -C₄ alkyl group, C₁ -C₄ alkoxy group, C₁ -C₄ alkylthio group, C₁ -C₄ haloalkyl group, C₁ -C₄ haloalkoxy group, C₁ -C₄ haloalkylthio group, C₂ -C₄ alkoxyalkyl group, C₂ -C₄ thioalkoxyalkyl group or NR⁷ R⁸, wherein R⁷ and R⁸ are independently a hydrogen atom, C₁ -C₄ alkyl group or C₁ -C₄ alkoxy group; and Z is a nitrogen atom or CH.
 7. A herbicidal composition which comprises a herbicidally effective amount of an N-(substituted amino)imide derivative represented by the formula (I) as an active ingredient and a carrier therefor, ##STR18## wherein, R¹ is a hydrogen atom, C₇ -C₉ alkyl group, C₁ -C₄ aralkyl group, C₁ -C₄ haloalkyl group, (C₁ -C₄ alkyl)carbonyl group or (C₁ -C₄ alkyl)sulfonyl group;A represents a structure selected from the group consisting of the following formulas (1), (2), (3) and (4) ##STR19## wherein R² and R³ in the (1) are independently a hydrogen atom or a C₁ -C₄ alkyl group, but not R² ═R³ ═H; X¹ and X² are independently a hydrogen atom, a halogen atom, a C₁ -C₄ alkyl group, C₁ -C₄ alkoxy group, C₁ -C₄ alkylthio group, C₁ -C₄ haloalkyl group, C₁ -C₄ haloalkoxy group, C₁ -C₄ haloalkylthio group, C₂ -C₄ alkoxyalkyl group, C₂ -C₄ thioalkoxyalkyl group or NR⁷ ; R⁸, wherein R⁷ and R⁸ are independently a hydrogen atom, C₁ -C₄ alkyl group or C₁ -C₄ alkoxy group; and Z is a nitrogen atom or CH. 